Cycling Puglia & Matera

Discover the heel of Italy by bike, taking a country-and-coast route from the cave town of Matera to baroque Lecce 

Cycling Puglia & Matera

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Trip Fee

$ 3.255

Single Room Difference

$ 1.238

Date

05 - 12 April 2026

Trip Information

Cycle the captivating region of Puglia, riding through olive groves and along the winding coast to stay in some of the most spectacular cities and towns in Italy. The adventure begins in the cave town of Matera, officially in the Basilicata region and beloved by film directors for its ancient beauty, before progressing to the fairytale trulli houses of Alberobello, the White City of Ostuni, and seaside Gallipoli. It ends in Lecce, known as the Florence of the South for its extraordinary collection of baroque landmarks.  

Activity Areas

Cycling
Cycling Bestsellers
E-Bike
Road Cycling

Region & Country & City

Europe: Italy, Matera, Puglia

Included in the Price

All accommodation: 7 Classic nights (5 hotel, 2 agriturismo/farmhouse)
- All breakfasts, one dinner
- Immersive itinerary with all transport and listed activities
- Expert tour leader to enhance your adventure
- Group arrival and departure transfers available
- Local bike hire of a fully serviced Velo Ville L 200 (touring/hybrid) bike

Not Included In The Price

Request a single room if required, purchase travel insurance and arrange any visas and vaccinations. On this trip, local taxes (approximately €10) are not included. If you want to upgrade to an e-bike, these are available for an additional cost.

Map

Itinerary

Day 1 Adventure begins in Matera

The town of Matera is a real jewel of southern Italy, and our hotel is just a short walk from the historic centre. There is usually time in the afternoon to wander through the narrow alleys of the town’s Unesco-listed cave-dwelling district and enjoy the unique atmosphere of this enchanting city. For millennia, inhabitants of this region have carved dwellings directly into ravines and gullies made of tuff (or tufa), a characteristic honey-coloured soft stone. These houses are called Sassi and are a Unesco World Heritage site. Matera is the only place in the world where people still live in the same houses as their ancestors did 9,000 years ago. Around 6pm, say ciao to your tour leader and fellow travellers, when we gather as a group to get to know each other and learn more about the adventures ahead. Your tour leader then ensures a big welcome over a group dinner. Want more time in Matera? Speak to your sales representative about adding extra nights. 

Day 2 Ride past the historic Sassi houses of Matera before heading to Alberobello

On leaving Matera, we pedal through the area that makes this town so special. Today's ride is mostly hilly with gentle ascents throughout, as we cycle on quiet rural roads among the picturesque Apulian countryside towards Alberobello. We’ll pass the lovely towns of Noci and Gioia del Colle plus fairytale trulli houses that have made the historic centre of Alberobello another World Heritage site.

Day 3 Cycle through the lush Valle d'Itria, past the fairytale trulli houses to the hilltop town of Ostuni

Today we cycle through the lush Valle d'Itria, one of the prettiest cultural and natural landscapes in southern Italy, to the hilltop town of Ostuni. The route is rolling throughout but much shorter than yesterday's ride. This allows us to enjoy the views at a more leisurely pace with plenty of opportunities for rest stops. Along the way we pass the wine town of Locorotondo and Cisternino, both known for their historic centres filled with whitewashed houses, narrow streets, churches and elegant piazzas. In the afternoon, we reach Ostuni, known as the White City thanks to the dazzling effect of its white buildings.

Day 4 Ride through quaint villages and country lanes to a typical masseria (renovated farmhouse) where we spend the night

We continue pedalling through tranquil country lanes to the town of Francavilla Fontana and on to Oria. A popular destination among Apulians, Oria is famous for its 13th-century castle and delightful historic centre of cobbled streets, whitewashed walls and beautiful architecture. We continue through the countryside to a masseria, a typical Apulian converted farmhouse and our accommodation for the night. The masseria is still a working farm and most of the produce grown here, from vegetables to olives and wheat, is used daily for the preparation of local dishes. Before dinner we will have the opportunity to taste some organic olive oil produced by the family that runs the farm and accommodation. Upgrade to a junior-suite today – speak to your sales representative for more details

Day 5 Cycle to the coast and swim in the crystal-clear sea before continuing towards Gallipoli with its old town on a rocky island

From the masseria we cycle towards the Ionian Coast and the beautiful town of Gallipoli, known as the Ionian Pearl with its old town on a rocky island offering fantastic views both to north and south. The town itself has many churches and narrow alleys and was the largest exporter of lamp oil made from olives in the 17th and 18th centuries. There are plenty of opportunities for swimming in the Ionian sea near the popular seaside resort of Porto Cesareo (weather permitting). Upgrade to a suite today – speak to your sales representative for more details

Day 6 Head towards the Adriatic Sea and the ancient town of Otranto

Leaving the Ionian Sea behind, we head across the peninsula to the Adriatic sea and the ancient Messapian town of Otranto, the easternmost point in Italy. Before dinner there will be time at leisure to explore the medieval town centre. Here the interesting architecture, views, sea-front restaurants and white sandy beaches make it one of the most picturesque towns in Puglia. Upgrade to a superior or deluxe room today – speak to your sales representative for more details

Day 7 Continue along the shoreline to the beautiful baroque city of Lecce

Today we follow the shoreline through innumerable olive groves to Lecce, the baroque masterpiece of southern Italy, in the heart of Puglia. Sometimes described as the Florence of the South, the city is an architectural gem, with sumptuous palazzi and churches. Today's ride is relatively short and easy, giving us time to stop for a last swim (seasonal) in Torre dell'Orso, a lovely bay surrounded by limestone cliffs with many ancient caves to discover. In Lecce, there will be free time to explore the historic centre before an optional farewell dinner.

Day 8 Adventure ends in Lecce

We enjoy our final breakfast of the adventure this morning. But if you’d like an extra day in Lecce to soak up the atmosphere of this elegant baroque city, speak to your sales representative about extending your stay.

Travel Dates

05 - 12 April 2026 $ 3.255

12 - 19 April 2026 $ 3.255

26 April - 03 May 2026 $ 3.570

03 - 10 May 2026 $ 3.450

10 - 17 May 2026 $ 3.255

17 - 24 May 2026 $ 3.450

24 - 31 May 2026 $ 3.255

31 May - 07 June 2026 $ 3.450

07 - 14 June 2026 $ 3.450

14 - 21 June 2026 $ 3.375

21 - 28 June 2026 $ 3.375

30 August - 06 September 2026 $ 3.255

06 - 13 September 2026 $ 3.255

13 - 20 September 2026 $ 3.330

20 - 27 September 2026 $ 3.330

27 September - 04 October 2026 $ 3.330

04 - 11 October 2026 $ 3.330

11 - 18 October 2026 $ 2.760

18 - 25 October 2026 $ 2.940

25 October - 01 November 2026 $ 3.255

04 - 11 April 2027 $ 3.525

11 - 18 April 2027 $ 3.525

25 April - 02 May 2027 $ 3.525

02 - 09 May 2027 $ 3.525

09 - 16 May 2027 $ 3.525

16 - 23 May 2027 $ 3.525

23 - 30 May 2027 $ 3.525

30 May - 06 June 2027 $ 3.720

06 - 13 June 2027 $ 3.720

13 - 20 June 2027 $ 3.525

20 - 27 June 2027 $ 3.525

29 August - 05 September 2027 $ 3.525

05 - 12 September 2027 $ 3.525

12 - 19 September 2027 $ 3.525

19 - 26 September 2027 $ 3.525

26 September - 03 October 2027 $ 3.525

03 - 10 October 2027 $ 3.525

10 - 17 October 2027 $ 3.525

17 - 24 October 2027 $ 3.525

24 - 31 October 2027 $ 3.525

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